Bradley,

You might want to look into hiring a Systems Admin. for the short term, until you feel comfortable adminning the server yourself. That way, you can rest assured that your sites are being taken care of by a competent person.

Another suggestion might be to look into managed VPS (Virtual Private Server). I would describe them as somewhere in between a full dedicated server and a reseller account, but with all of the control of a dedicated server with at least half the price.

-- Jonathan